Metal-free synthesis of 2-substituted (N, O, C) benzothiazoles via an intramolecular C-S bond formation

J Comb Chem. 2010 Jul 12;12(4):422-9. doi: 10.1021/cc9001839.

Abstract

An efficient, economical, and convenient method was developed for the preparation of 2-substituted (N, O, C) benzothiazoles from N'-substituted-N-(2-halophenyl)thioureas, O'-substituted-N-(2-halophenyl) carbamothioates, or N-(2-halophenyl) thioamides via a base-promoted cyclization in dioxane without any transition metal. A one-pot variant combining the synthesis of the thiourea and the cyclization was also demonstrated. High yields were obtained, and a variety of functional groups were tolerated under these conditions. Transition-metal-free, mild reactive conditions, wide application scope, and shorter reaction times make this method superior to the reported methods for the synthesis of 2-substituted benzothiazoles and suitable for combinatorial format.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / chemistry
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Molecular Structure
  • Stereoisomerism

Substances

  • Benzothiazoles